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Benzimidazolyl thiazolidinone compounds and synthesis method thereof

A benzimidazole-based, thiazolidinedione technology, applied in the direction of organic chemistry, drug combination, metabolic diseases, etc., can solve the problems of low fat solubility, difficult to penetrate the blood-brain barrier, unable to reach diabetic encephalopathy, etc., and achieve fat solubility. Strong, easy to cross the blood-brain barrier effect

Inactive Publication Date: 2011-11-23
FOURTH MILITARY MEDICAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the disadvantages of the above-mentioned TZD PPAR-γ agonists are that their fat solubility is not high, it is difficult to penetrate the blood-brain barrier, they cannot effectively improve the insulin sensitivity in the brain, and they cannot directly treat diabetic encephalopathy.

Method used

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  • Benzimidazolyl thiazolidinone compounds and synthesis method thereof
  • Benzimidazolyl thiazolidinone compounds and synthesis method thereof
  • Benzimidazolyl thiazolidinone compounds and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Example 1: Synthesis of 5-((4-((1H-benzoimidazolyl)methoxy)phenyl)methyl)thiazole-2,4-dione (HJ-2)

[0050] (1) The synthesis of compound 2-chloromethyl-1H-benzimidazole, the synthetic steps are as follows:

[0051]

[0052] Add 0.54g (5.0mmol) of o-phenylenediamine, 0.567g (6.0mmol) of chloroacetic acid and 30mL of 1mol / L hydrochloric acid into a 50mL three-neck flask equipped with a reflux condenser, stir with a magnet, raise the temperature to 90°C for 12h, and cool After reaching room temperature, the reaction solution was poured into a mixed solution of ice and water, and the pH was adjusted to 8 with 1 mol / L sodium hydroxide, and a flesh-colored powder precipitated out. Suction filtration and drying yielded 0.76 g of crude product with a yield of 91.30%.

[0053] Mass spectrum MS, ESI-: 166.82 (M-H), (calcd.166.61);

[0054] Nuclear magnetic 1H NMR (DMSO) δ (ppm) 4.92 (s, 2H), 7.20-7.22 (m, 2H), 7.55-7.57 (m, 2H).

[0055] (2) Synthesis of compound 5-(4-hydr...

Embodiment 2

[0070] Example 2: Synthesis of 5-((4-((5-methyl-1H-benzoimidazolyl)methoxy)phenyl)methyl)thiazole-2,4-dione (HJ-4)

[0071] (1) The synthesis of compound 2-(chloromethyl)-5-methyl-1H-benzimidazole is similar to Example 1 step (1), except that 3-methyl o-phenylenediamine replaces o-phenylenediamine , yield 70.00%.

[0072] (2) For the synthesis of compound 5-(4-hydroxybenzylidene)thiazole-2,4-dione, see step (2) of Example 1.

[0073] (3) Synthesis of compound 5-(4-hydroxybenzyl)thiazole-2,4-dione See step (3) of Example 1.

[0074] (4) 5-((4-((5-methyl-1H-benzimidazolyl)methoxy)phenyl)methyl)thiazole-2,4-dione (HJ-4) and Example 1 step

[0075] (4) similar, yield 80.30%.

Embodiment 3

[0076] Example 3: Synthesis of 5-((4-((1-methyl-1H-benzoimidazolyl)methoxy)phenyl)methyl)thiazole-2,4-dione (HJ-6)

[0077] (1) The synthesis of compound 2-(chloromethyl)-5-methyl-1H-benzimidazole is similar to Example 1 step (1), except that N-methyl o-phenylenediamine replaces o-phenylenediamine , yield 70.00%.

[0078] (2) For the synthesis of compound 5-(4-hydroxybenzylidene)thiazole-2,4-dione, see step (2) of Example 1.

[0079] (3) Synthesis of compound 5-(4-hydroxybenzyl)thiazole-2,4-dione See step (3) of Example 1.

[0080] (4) 5-((4-((1-methyl-1H-benzimidazolyl)methoxy)phenyl)methyl)thiazole-2,4-dione (HJ-6) and Example 1 Step (4) is similar, yield 90.00%.

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Abstract

The invention relates to benzimidazolyl thiazolidinone compounds and a synthesis method thereof. The compounds have a structure shown by a general formula (I), wherein R1 and R2 may be methyl, ethyl, benzyl, alkyl or hydrogen; and n is an integer between 1 and 5. The benzimidazolyl thiazolidinone compounds provided by the invention are high-affinity ligands having specificity against peroxisome proliferator-activated receptor (PPAR-gamma), by improving glucose absorption by cells and lowering output of glycogen, the sensitivity of cells to insulin is increased and the antagonism of tissues against glucose; and the compounds, compared with the conventional thiazolidinones PPAR-gamma activating agent, has high lipid solubility, is easier to pass through blood brain barrier, improves the sensitivity of insulin in brain, and can be used for treating neurological diseases caused by diabetes and neuroprotection.

Description

technical field [0001] The invention belongs to the field of synthesizing new drugs for treating diabetic encephalopathy, in particular to thiazoledione compounds with benzimidazole groups and their synthesis methods. Background technique [0002] Diabetic encephalopathy is one of the chronic complications of diabetes, which affects important functions such as cognition and memory of patients, and seriously affects the quality of life of patients. It has attracted more and more attention in recent years. The pathogenesis of diabetic encephalopathy is relatively complicated. Brain function damage caused by diabetes itself and senile encephalopathy are intertwined. In addition, there are still some unexplained pathogenesis, so the treatment of diabetic encephalopathy is also very complicated. [0003] The treatment of diabetic encephalopathy is mainly on the basis of controlling blood sugar, supplemented by drugs to improve brain cell function. Improving blood rheology, contr...

Claims

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Application Information

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IPC IPC(8): C07D417/12A61P3/10A61P25/28A61P25/00
Inventor 招明高韩洁张俊吴玉梅刘水冰李小强
Owner FOURTH MILITARY MEDICAL UNIVERSITY
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